SYNTHESIS OF AROMATIC S-SUBSTITUTED DERIVATIVES OF N-ACETYL-L-CYSTEINE

A new method for the preparation of aromatic, S-substituted derivatives of N-acetyl-L-cysteine is described. The method involves nucleophilic substitution of aromatic iodides by N-acetyl-L-cysteine in the presence of Cu(I) iodide, and provides the 1st example of nucleophilic substitution of unactiva...

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Bibliographic Details
Published inAustralian journal of chemistry Vol. 38; no. 6; pp. 899 - 904
Main Authors HICKMAN, RJS, CHRISTIE, BJ, GUY, RW, WHITE, TJ
Format Journal Article
LanguageEnglish
Published CLAYTON Csiro Publishing 01.01.1985
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:A new method for the preparation of aromatic, S-substituted derivatives of N-acetyl-L-cysteine is described. The method involves nucleophilic substitution of aromatic iodides by N-acetyl-L-cysteine in the presence of Cu(I) iodide, and provides the 1st example of nucleophilic substitution of unactivated aromatic halides by N-acetyl-S-(3-thienyl)-L-cysteine from 2-iodothiophen and 3-iodothiophen, respectively. In addition, the method was successfully applied to iodobenzene and 1-iodonaphthalene. A product yield of .apprx. 30% was obtained in each case.
ISSN:0004-9425
1445-0038
DOI:10.1071/CH9850899